Synthesis and antimicrobial properties of new 2-((4-ethylphenoxy)methyl)benzoylthioureas
-
Carmen Limban
,
Alexandru Missir
Abstract
New acylthiourea derivatives, 2-((4-ethylphenoxy)methyl)-N-(phenylcarbamothioyl)benzamides, were tested by qualitative and quantitative methods on various bacterial and fungal strains and proved to be active at low concentrations against Gram-positive and Gram-negative bacteria as well as fungi. These compounds were prepared by the reaction of 2-((4-ethylphenoxy)methyl)benzoyl isothiocyanate with various primary aromatic amines, and were characterised by melting point and solubility. The structures were identified by elemental analysis, 1H and 13C NMR, and IR spectral data. The level of antimicrobial activity of the new 2-((4-ethylphenoxy)methyl)benzoylthiourea derivatives was dependent on the type, number and position of the substituent on the phenyl group attached to thiourea nitrogen. The iodine and nitro substituents favoured the antimicrobial activity against the Gram-negative bacterial strains, while the highest inhibitory effect against Gram-positive and fungal strains was exhibited by compounds with electron-donating substituents such as the methyl and ethyl groups.
[1] Balotescu, M. C., Limban, C., Missir, A. V., Chirita, I. C., & Nitulescu, G. M. (2007). The synthesis and biological activities of some new 2-(4-methoxy-phenoxymethyl)benzoic acid thioureides. Revista de Chimie (Bucureşti), 58, 1064–1068. Suche in Google Scholar
[2] Balotescu, M. C., Oprea, E., Petrache, L. M., Bleotu, C., & Lazar, V. (2005). Antibacterial, antifungal and cytotoxic activity of salvia officinalis essential oil and tinctures. Romanian Biotechnological Letters, 10, 2481–2481. Suche in Google Scholar
[3] Boşcencu, R., Nacea, V., Limban, C., Missir, A., & Socoteanu, R. (2007). Combinatţii complexe ale unor metale tranzitţionale cu noi tioureide N,N′-disubstituite. Revista de Chimie (Bucureşti), 58, 16–19. Suche in Google Scholar
[4] Chow, A. W. (1984). U.S. Patent No. 4438135. Washington, D.C., USA: U.S. Patent and Trademark Office. Suche in Google Scholar
[5] Clinical and Laboratory Standards Institute (2007). Performance standards for antimicrobial susceptibility testing. Seventeenth Informational Supplement M100-S17. Wayne, PA, USA: CLSI. Suche in Google Scholar
[6] Cunha, S., Macedo, F. C., Jr., Costa, G. A. N., Rodrigues, M. T., Jr., Verde, R. B. V., de SouzaNeta, L.C., Vencato, I., Lariucci, C., & Sá, F. P. (2007). Antimicrobial activity and structural study of disubstituted thiourea derivatives. Monatshefte für Chemie, 138, 511–516. DOI: 10.1007/s00706-007-0600-y. http://dx.doi.org/10.1007/s00706-007-0600-y10.1007/s00706-007-0600-ySuche in Google Scholar
[7] Desai, K. R., & Desai, P. H. (1989). Synthesis and antibacterial activity of 2,4-bis(4-methoxyanilino)-6-(N-arylthioureido-N’-aminoacyl)-s-triasine derivatives. Journal of the Institution of Chemists (India), 61, 19–20. Suche in Google Scholar
[8] Hammam, A. S., Youssef, M. S. K., Atta, F. M., & Mohamed, T. A. (2007). Synthesis of new triphenodithiazine- and in-dolocarbazolediones of biological interest. Chemical Papers, 61, 292–299. DOI: 10.2478/s11696-007-0036-1. http://dx.doi.org/10.2478/s11696-007-0036-110.2478/s11696-007-0036-1Suche in Google Scholar
[9] Jia, X.-S., Wang, Y.-L., Li, Y.-F., He, F.-S., & Shan, Y.-F. (1993). Synthesis of 1-aroyl-3-(4-benzosulfonamidopyrimidine)-thioureas. Chinese Journal of Organic Chemistry, 13, 250–252. Suche in Google Scholar
[10] Kapoor, K. K., Somal, P., Gupta, R., & Kachroo, P. L. (1991). Synthesis and antimicrobial activity of some 5-aryl-2-[N-(5-nitrofurfurylidene)amino]- and 5-aryl-2-(N-thiocarbamoylamino)-1,3,4-oxadiazoles. Journal of the Indian Chemical Society, 68, 104–106. Suche in Google Scholar
[11] Ke, S.-Y., & Xue, S.-J. (2006). Synthesis and herbicidal activity of N-(o-fluorophenoxyacetyl)thioureas derivatives and related fused heterocyclic compounds. ARKIVOC, 2006(x), 63–68. 10.3998/ark.5550190.0007.a08Suche in Google Scholar
[12] Kurt, G., Sevgi, F., & Mercimek, B. (2009). Synthesis, characterization, and antimicrobial activity of new benzoylthiourea ligands. Chemical Papers, 63, 548–553. DOI: 10.2478/s11696-009-0055-1. http://dx.doi.org/10.2478/s11696-009-0055-110.2478/s11696-009-0055-1Suche in Google Scholar
[13] Lazar, V., Balotescu, M. C., Moldovan, L., Vasilescu, G., Petrache, L. M., Bulai, D., & Cernat, R. (2005). Comparative evaluation of qualitative and quantitative methods used in the study of antifungal and antibacterial activity of hydroalcoholic vegetal extracts. Romanian Biotechnological Letters, 10, 2225–2232. Suche in Google Scholar
[14] Limban, C., Balotescu Chifiriuc, M. C., Missir, A. V., Chiriţă, I., & Bleotu, C. (2008a). Antimicrobial activity of some new thioureides derived from 2-(4-chlorophenoxymethyl)benzoic acid. Molecules, 13, 567–580. DOI: 10.3390/molecules13030 567. http://dx.doi.org/10.3390/molecules13030567Suche in Google Scholar
[15] Limban, C., Missir, A., & Chirita, I. (2004). Noi tioureide ale acidului 2-(fenoximetil)-benzoic. Nota II. Farmacia, 52, 7–12. Suche in Google Scholar
[16] Limban, C., Missir, A., & Chirita, I. (2000). Noi tioureide ale acidului 2-(fenoximetil)-benzoic. Nota I. Farmacia, 48, 73–78. Suche in Google Scholar
[17] Limban, C., Missir, A. V., Chiriţă, I. C., Drăghici, B., Chifiriuc, M. C., & Bleotu, C. (2009b). RO Patent No. 122638. Bucharest, Romania: Romanian State Office for Inventions and Trademarks. Suche in Google Scholar
[18] Limban, C., Missir, A. V., Chiriţă, I. C., Bădiceanu, C. D., Drăghici, C., Balotescu, M. C., & Stamatoiu, O. (2008b). New thioureides of 2-(4-methyl-phenoxymethyl)-benzoic and 2-(4-methoxy-phenoxymethyl)-benzoic acids with biological activity. Revue Roumaine de Chimie, 53, 595–602. Suche in Google Scholar
[19] Limban, C., Missir, A. V., Chirită, I. C., Ilie, C., & Căproiu, M. T. (2008c). Studies on synthesis of some novel thioureides of 2-(4-methyl-phenoxymethyl)benzoic acid with antimicrobial activity. Revista de Chimie (Bucureşti), 59, 1136–1139. 10.37358/RC.08.10.1983Suche in Google Scholar
[20] Limban, C., Missir, A., Chirita, I., Nitulescu, G. M., Caproiu, M. T., & Ilie, C. (2008d). The synthesis and characterization of some new thioureides of 2-(4-methyl-phenoxymethyl)benzoic acid with antimicrobial activity. Revista de Chimie (Bucure şti), 59, 1245–1248. 10.37358/RC.08.11.2012Suche in Google Scholar
[21] Limban, C., Missir, A. V., Chirita, I. C., Nitulescu, G. M., Ilie, C., & Caproiu, M. T. (2009a). Some new 2-(4-ethylphenoxymethyl) benzoic acid thioureides: Synthesis and spectral characterisation. Revista de Chimie (Bucureşti), 60, 657–661. Suche in Google Scholar
[22] Müller, J., Limban, C., Stadelmann, B., Missir, A. V., Chirita, I. C., Chifiriuc, M. C., Nitulescu, G. M., & Hemphill, A. (2009). Thioureides of 2-(phenoxymethyl)benzoic acid 4-R substituted: A novel class of anti-parasitic compounds. Parasitology International, 58, 128–135. DOI: 10.1016/j.parint.2008. 12.003. http://dx.doi.org/10.1016/j.parint.2008.12.00310.1016/j.parint.2008.12.003Suche in Google Scholar PubMed
[23] Nacea, V., Boscencu, R., Missir, A., Limban, C., & Barbuceanu, S. (2005). Sinteza şi caracterizarea unor combinaţi complexe ale Cu(I) şi Cu(II) cu noi tioureide N,N′-disubstituite. Revista de Chimie (Bucureşti), 56, 68–71. Suche in Google Scholar
[24] National Committee for Clinical Laboratory Standards (2000). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically (5th ed.). Approved standard M7-A5. Wayne, PA, USA: NCCLS. Suche in Google Scholar
[25] National Committee for Clinical Laboratory Standards (2002). Reference method for broth dilution antifungal susceptibility testing of filametous fungi. Approved standard M38-A. Wayne, PA, USA: NCCLS. Suche in Google Scholar
[26] Olar, R., Badea, M., Cristurean, E., Lazar, V., Cernat, R., & Balotescu, C. (2005). Thermal behavior, spectroscopic and biological characterization of Co(II), Zn(II) and Pt(II) complexes with N,N-dimethylbiguanide. Journal of Thermal Analysis and Calorimetry, 80, 451–455. DOI: 10.1007/s10973-005-0676-8. http://dx.doi.org/10.1007/s10973-005-0676-810.1007/s10973-005-0676-8Suche in Google Scholar
[27] Saeed, A., Rafique, H., Hameed, A., & Rasheed, S. (2008). Synthesis and antibacterial activity of some new 1-aroyl-3-(substituted-2-benzothiazolyl)thioureas. Pharmaceutical Chemistry Journal, 42, 191–195. DOI: 10.1007/s11094-008-0094-x. http://dx.doi.org/10.1007/s11094-008-0094-x10.1007/s11094-008-0094-xSuche in Google Scholar
[28] Saeed, A., Shaheen, U., Hameed, A., & Naqvi, S. Z. H. (2009). Synthesis, characterization and antimicrobial activity of some new 1-(fluorobenzoyl)-3-(fluorophenyl)thioureas. Journal of Fluorine Chemistry, 130, 1028–1034. DOI: 10.1016/j.jfluchem.2009.09.003. http://dx.doi.org/10.1016/j.jfluchem.2009.09.00310.1016/j.jfluchem.2009.09.003Suche in Google Scholar
[29] Sun, C., Huang, H., Feng, M., Shi, X., Zhang, X., & Zhou, P. (2006). A novel class of potent influenza virus inhibitors: Polysubstituted acylthiourea and its fused heterocycle derivatives. Bioorganic & Medicinal Chemistry Letters, 16, 162–166. DOI: 10.1016/j.bmcl.2005.09.033. http://dx.doi.org/10.1016/j.bmcl.2005.09.03310.1016/j.bmcl.2005.09.033Suche in Google Scholar PubMed
[30] Zhong, Z., Xing, R., Liu, S., Wang, L., Cai, S., & Li, P. (2008). Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro. Carbohydrate Research, 343, 566–570. DOI: 10.1016/j.carres.2007.11.024. http://dx.doi.org/10.1016/j.carres.2007.11.02410.1016/j.carres.2007.11.024Suche in Google Scholar PubMed
[31] Zikán, V., Sluka, J., Daněk, J. (1988). CS Patent No. 8800122. Prague, Czechoslovakia: Czechoslovak Office for Trademarks and Inventions. Suche in Google Scholar
© 2010 Institute of Chemistry, Slovak Academy of Sciences
Artikel in diesem Heft
- Application of polyaniline as an efficient and novel adsorbent for azo dyes removal from textile wastewaters
- Enzymatic synthesis and analytical monitoring of terpene ester by 1H NMR spectroscopy
- Effect of fiber modification with carboxymethyl cellulose on the efficiency of a microparticle flocculation system
- Synthesis, crystal structure, and thermal analysis of a copper(II) complex with imidazo[4,5-f]1,10-phenantroline
- Hydrothermal synthesis of core-shell structured PS@GdPO4:Tb3+/Ce3+ spherical particles and their luminescence properties
- Optical characterisation of organosilane-modified nanocrystalline diamond films
- Synthesis, optical, and spectroscopic characterisation of substituted 3-phenyl-2-arylacrylonitriles
- A new group of potential antituberculotics: N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides
- Synthesis and antimicrobial properties of new 2-((4-ethylphenoxy)methyl)benzoylthioureas
- Synthesis, characterisation, and biological activity of three new amide prodrugs of lamotrigine with reduced hepatotoxicity
- Comparative study of CTAB adsorption on bituminous coal and clay mineral
- Density of the systems (NaF/AlF3)—AlPO4 and (NaF/AlF3)—NaVO3
- Semiquinol and phenol compounds from seven Senecio species
- Determination of the enthalpy of fusion of K3NbO2F4
Artikel in diesem Heft
- Application of polyaniline as an efficient and novel adsorbent for azo dyes removal from textile wastewaters
- Enzymatic synthesis and analytical monitoring of terpene ester by 1H NMR spectroscopy
- Effect of fiber modification with carboxymethyl cellulose on the efficiency of a microparticle flocculation system
- Synthesis, crystal structure, and thermal analysis of a copper(II) complex with imidazo[4,5-f]1,10-phenantroline
- Hydrothermal synthesis of core-shell structured PS@GdPO4:Tb3+/Ce3+ spherical particles and their luminescence properties
- Optical characterisation of organosilane-modified nanocrystalline diamond films
- Synthesis, optical, and spectroscopic characterisation of substituted 3-phenyl-2-arylacrylonitriles
- A new group of potential antituberculotics: N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides
- Synthesis and antimicrobial properties of new 2-((4-ethylphenoxy)methyl)benzoylthioureas
- Synthesis, characterisation, and biological activity of three new amide prodrugs of lamotrigine with reduced hepatotoxicity
- Comparative study of CTAB adsorption on bituminous coal and clay mineral
- Density of the systems (NaF/AlF3)—AlPO4 and (NaF/AlF3)—NaVO3
- Semiquinol and phenol compounds from seven Senecio species
- Determination of the enthalpy of fusion of K3NbO2F4
